Labile crosslinked hyaluronic acid via urethane formation using bis(β-isocyanatoethyl) disulphide with tuneable physicochemical and immunomodulatory properties

Zamboni, Fernanda; Ryan, Elizabeth J.; Culebras, Mario; Collins, Maurice N.

doi:10.1016/j.carbpol.2020.116501

Cited by 64 publications

(34 citation statements)

References 40 publications

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“…Hydrogels are showing enormous potential due to their advantageous properties such as tunable time-dependent swelling behavior, biocompatibility, tunable mechanical behavior, and their ease of chemical modification. 5 − 8 Hydrogels are typically defined as three-dimensional, hydrophilic, polymer networks capable of absorbing large amounts of water or biological fluids. Synthetic polymers such as poly(hydroxyalky1 methacrylates), 9 , 10 poly(acrylamide), 11 , 12 poly(methacrylamide), and poly( N -vinyl-2-pyrrolidone) 13 , 14 have been extensively used in the preparation of hydrogels.…”

Section: Introductionmentioning

confidence: 99%

Wood-Derived Hydrogels as a Platform for Drug-Release Systems

Culebras

Barrett

Pishnamazi

et al. 2021

ACS Sustainable Chem. Eng.

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135

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Wood (cellulose and lignin)-based hydrogels were successfully produced as platforms for drug-release systems. Viscoelastic and cross-linking behaviors of precursor solutions were tuned to produce highly porous hydrogel architectures via freeze-drying. Pore sizes in the range of 100–160 μm were obtained. Varying lignin molecular structure played a key role in tailoring swelling and mechanical performance of these gels with organosolv-type lignin showing optimum properties due to its propensity for intermolecular cross-linking, achieving a compressive modulus around 11 kPa. Paracetamol was selected as a standard drug for release tests and its release rate was improved with the presence of lignin (50% more compared to pure cellulose hydrogels). This was attributed to a reduction in molecular interactions between paracetamol and cellulose. These results highlight the potential for the valorization of lignin as a platform for drug-release systems.

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Section: Introductionmentioning

confidence: 99%

Wood-Derived Hydrogels as a Platform for Drug-Release Systems

Culebras

Barrett

Pishnamazi

et al. 2021

ACS Sustainable Chem. Eng.

Self Cite

135

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“…Currently, lignin has become the focus of many studies in the field of hydrogel development due to its inherent properties such as biocompatibility, biodegradability, low toxicity, and importantly its susceptibility to enzymatic degradation [20]. For this reason, the formation of hydrogels based on lignin represents an excellent valorization route for lignin waste streams through biomedical and biotechnological applications, including enzyme immobilization, tissue engineering (TE), drug delivery systems, and biosensors, [21][22][23][24][25][26][27][28]. In particular, controlled drug release is an area of interest in pharmaceutical science gaining considerable attention within the research community.…”

Section: Introductionmentioning

confidence: 99%

Facile Tailoring of Structures for Controlled Release of Paracetamol from Sustainable Lignin Derived Platforms

et al. 2021

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Nowadays, sustainable materials are receiving significant attention due to the fact that they will be crucial for the development of the next generation of products and devices. In the present work, hydrogels have been successfully synthesized using lignin which is non-valorized biopolymer from the paper industry. Hydrogels were prepared via crosslinking with Poly(ethylene) glycol diglycidyl ether (PEGDGE). Different crosslinker ratios were used to determine their influence on the structural and chemical properties of the resulting hydrogels. It has been found that pore size was reduced by increasing crosslinker amount. The greater crosslinking density increased the swelling capacity of the hydrogels due to the presence of more hydrophilic groups in the hydrogel network. Paracetamol release test showed higher drug diffusion for hydrogels produced with a ratio lignin:PEGDGE 1:1. The obtained results demonstrate that the proposed approach is a promising route to utilize lignocellulose waste for producing porous materials for advanced biomedical applications in the pharmacy industry.

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“…Specifically, recent studies have reported low (LMW) and high-molecular-weight HA (HMW) cross-linked by urethane bond formation, using a diisocyanate (BIED), which has a better profile than commonly used aryl di-isocyanates. These novel cross-linked hydrogels have shown potential use for vaccine administration (LMW HA) and cell encapsulation to reduce immune rejection of transplanted cells (HMW HA) [32]. Furthermore, this new material showed interesting bacteriostatic properties towards Staphylococcus (S.) aureus [33].…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, Characterization, and In Vitro Evaluation of a New Cross-Linked Hyaluronic Acid for Pharmaceutical and Cosmetic Applications

et al. 2021

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Hyaluronic acid (HA), an excellent biomaterial with unique bio properties, is currently one of the most interesting polymers for many biomedical and cosmetic applications. However, several of its potential benefits are limited as it is rapidly degraded by hyaluronidase enzymes. To improve the half-life and consequently increase performance, native HA has been modified through cross-linking reactions with a natural and biocompatible amino acid, Ornithine, to overcome the potential toxicity commonly associated with traditional linkers. 2-chloro-dimethoxy-1,3,5-triazine/4-methylmorpholine (CDMT/NMM) was used as an activating agent. The new product (HA–Orn) was extensively characterized to confirm the chemical modification, and rheological analysis showed a gel-like profile. In vitro degradation experiments showed an improved resistance profile against enzymatic digestions. Furthermore, in vitro cytotoxicity studies were performed on lung cell lines (Calu-3 and H441), which showed no cytotoxicity.

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Labile crosslinked hyaluronic acid via urethane formation using bis(β-isocyanatoethyl) disulphide with tuneable physicochemical and immunomodulatory properties

Cited by 64 publications

References 40 publications

Wood-Derived Hydrogels as a Platform for Drug-Release Systems

Wood-Derived Hydrogels as a Platform for Drug-Release Systems

Facile Tailoring of Structures for Controlled Release of Paracetamol from Sustainable Lignin Derived Platforms

Design, Synthesis, Characterization, and In Vitro Evaluation of a New Cross-Linked Hyaluronic Acid for Pharmaceutical and Cosmetic Applications

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